23 going on 60.

June 20, 2012 5:59 AM

Help me dress myself, 23-year-old-going-on-little-old-lady edition.

I am 23, but find myself drawn to clothes/styles that are typically for older people. Cardigans, mom jeans, Dansko clogs, frumpy old-man sweaters and glasses -- the list goes on.

I would like to embrace being a relatively slender, relatively fit, relatively attractive twenty-something and stop dressing like my mother and/or grandfather, but I don't know what to look for/how to do it. I dislike the busy prints that seem to be in vogue these days, and would prefer a more classic/timeless look.

1. Is it possible to be timeless/classic and not frumpy?
1a. If so, how? Links to specific items or outfits would be appreciated.

2. If you are a big-busted, small-waisted ladyperson, how do you find shirts that flatter both the top and bottom half of your torso while maintaining a workplace-appropriate look (i.e., not too tight, not too cleavage-y)?

3. Ideally, I would like to turn heads without skanking it up. How to go about this?

posted by coppermoss to clothing, beauty, & fashion (20 answers total)

1. I have similar taste & shop at PinUpGirl almost exclusively. At discount stores (ex. TJ Maxx, Marshalls) I sometimes find Calvin Klein items which also fit my taste/figure. I've heard that J. Crew now has a Mad Men -influenced line, which sounds up our alley as well.

2. I *rarely* find button-up shirts that don't pull at the bust or reveal too much. I tend to stick to sleeveless tops with a shrug or fitted blazer (or, yes, plain cardigan, but one made of material which hangs rather than bunches).

3. I always get compliments, rarely show any cleavage, and never more than an inch or two of skin above the knee. Granted, I'm a good 15 years older than you, so you can get away with a bit more, at least socially if not in the workplace.

Good luck, and enjoy - I went through a similar metamorphosis myself around your age. The Mad Men craze has made finding suitable clothing much easier, FWIW.
posted by pammeke at 6:09 AM on June 20, 2012 [2 favorites]

ModCloth is very hip with the kids these days and also has a lot of classic/vintage inspired things that fit the general aesthetic you're talking about.
posted by sonika at 6:14 AM on June 20, 2012 [2 favorites]

1. Clothes that really fit. This is the answer to not looking frumpy. Try on EVERYTHING and don't settle for things that don't fit (and can't be tailored to fit, but that's hard to figure out at first so mostly just look for things that really fit). And I'm sorry, because they are so great in some ways, but Dansko clogs are always going to look frumpy. Put them away, at least for the summer! (If you need to wear them for work, wear them for work only.)

Also: always wear at least some color.

2. The correct answer is to go to a tailor and get your shirts taken in at the waist. I never do this. And I look frumpier as a result. So, do as I say, not as I do. The other answer is to wear knit shirts and sweaters. Also I find I need to go with shorter shirts than are currently popular. Those looooong layering t-shirts and tanks that end at the hip or below hide my waist, and not in a good way.

3. Pencil skirts.
posted by mskyle at 6:20 AM on June 20, 2012 [4 favorites]

As a fellow hourglassy person, Oxfords are, alas, my shirt nemesis. My solution is to make my own, but if that's not an option for you, check out Etsy Alchemy or a dressmaker. you should be able to pay $50/shirt and have something that looks really good. taking in shirts at the waist is better than nothing at all, but I tend to find that commercial shirts are typically cut for a B-ish cup - so if the shoulders fit, the bust will be too small for larger breasts, and if the bust fits, the shirt is sloppy at the shoulders. recutting shoulders is sufficiently complex that you might as well start from scratch.

if you have shirts made, always, always have the buttons placed like this: one at the collar, one at an appropriate lowest-button point, one at the greatest stress area across your bust, the rest distributed in between. It makes no sense to me that there is usually a big gaping gap across the fullest part of your chest. what is up with that?

if your shirts pull just a little across your bust but fit well otherwise, sew a little hook and eye there so it's hidden under the button band and takes most of the stress.

also: high-waisted stuff is your friend. I would never have believed how flattering high waisted clothes can be, but if you tuck the right top into cute high-waisted pants or curve skimming skirts, you'll be so va va boom you won't know what to do with yourself.
posted by peachfuzz at 6:48 AM on June 20, 2012 [5 favorites]

Pinterest and Polyvore might be good for figuring out exactly what items you like and how to incorporate those items into an outfit. I just searched for "timeless tailored" on Pinterest and found some cute stuff. Watching What Not to Wear was really useful for me in learning about the importance of tailoring and choosing items that flatter my figure. So yes, you can absolutely look classic and not frumpy. And for question 2, Brooks Brothers non-iron tailored shirts work for me. I bought a white one and a blue one years ago and wear them all the time with skirts and a cute necklace or bracelet and frequently get compliments. Those shirts might not be the right fit for you, but buying one or two non-iron buttondowns and then getting them tailored so they fit you perfectly makes getting dressed really easy. A few flattering dresses help too and then there's no worrying about coordinating separates. I'll often add a belt or a sash to a dress to emphasize my waist and customize the fit a little. And the secret for question 3 is buying good-quality, figure-flattering basics, and then putting them together with eye-catching accessories so that you look polished and together. It's pretty easy once you get the formula down. You'll be stunning!
posted by k96sc01 at 7:04 AM on June 20, 2012

May I suggest Danskos/Sanitas in the maryjane style with skinny jeans? Adorable, come on! Like everyone else said, the key is to wear well-fitting duds. I have always been kind of a frump myself, glasses, Danskos, cardigans, allthe rest (minus the mom jeans, though), and Mad Men as well as the rise of geek chic aesthetic have definitely made it easier to get a look that IS classic and maybe a little bit frump-tastic as well as head turning.

This may be a no brainer, but
I dont think anyone mentioned belts. Im on the bigger side on top and one of the things that can dress up a boring skirt, tee, and cardigan look is to wear a nice skinny colored belt over the open cardigan so it gives your shape the ability to shine without being super tight or form fitting. I also like the sheath dresses that are everywhere now - you can get plain colored ones at Target or Banana Republic that are really basic and can go literally from work to a wedding. I have lots of belts and scarves that I can tie around the waist, sometimes more around the empire waist area, and it gives me a little definition when the dress might have to be a little bigger to accommodate my bust where it might also be a little baggies around the true waist.
And seriously, classic five pocket skinny jeans (can even be high waisted if you are that tiny of a waist!) with a cuff or little bit of bunch around the ankles (I like to buy longer jeans for this reason), or
cigarette style khakis and Danskos or some cheap Walmart/Target/Payless flats - sooo cute, very classic.
posted by takoukla at 7:09 AM on June 20, 2012

Hello young hour-glass! As for button-blouses, you might want to write them off of your list. I wish it hadn't taken me 30 years to do it.

You indicate that you're more of a Classic/Timeless kind of person.

You have some choices. Here are some brands that are in your wheelhouse:

Tommy Hilfiger
Ralph Lauren
Jones New York
Banana Republic
Ann Taylor
Talbots

You need to skip the junior department, you're in Misses now. I like shopping at Macys because they have good sales and coupons. Look in your Saturday paper. There they are.

I like Real Simple wardrobe suggestions. Very classic/timeless. Here is a helpful checklist.

Another thing it took me too long to discover was tailoring. Even if I only spent $15 on an item, it's worth it to have your jeans professionally hemmed. Remember to bring the shoes you want to wear with those pants, with you.

I also have to have certain pants altered to fit in the waist and booty correctly. Well worth it.

Don't try and buy a wardrobe all at once. Have a list of what you need, and always be on the lookout for deals. Your need for black and white shirts will never cease, so if you see a great one on sale, snag it. The same with great jeans. Find the brand and style you like and buy them in different washes or colors.

There is a thing called the Moscow Rule of Shopping. It comes from the old Soviet days, where you have to act as though you'll never have the opportunity to get it again, so get it now. Don't take too long to ponder certain purchases. If a great pair of shoes isn't on sale, just get them.

As for shoes, if you want something elegant and comfortable, rather than Danso, look at Born, Sofft and of all things, Cole Haan/Nike. They make heels that are as comfortable as sneakers. About $200 a pair, but one great pair of black pumps that are comfy is totally worth it. If you have the dough, Ferragamo.

You will want to be on the lookout for a signature piece. Perhaps you invest in an Hermes scarf. Maybe you get yourself a Diane Von Furstenburg wrap dress (and you should!) Check out a vintage store for a lovely jacket that you can wear with jeans or dressy slacks. Something that only you would have.

As for a handbag, I like Tignanello, can be had rather cheaply at Macys on sale, good quality leather, up to date shapes. Fun colors.

Go through magazines and see what attracts you. In Style shows the trends and composes outfits based on them. Real Simple does too.

Fashion is fun!
posted by Ruthless Bunny at 7:09 AM on June 20, 2012 [3 favorites]

Also, glasses are in these days and lots of people look awesome in giant plastic ones, but there are definitely more low profile conservative ones that are more on the classic side that are still not wire frames.
posted by takoukla at 7:11 AM on June 20, 2012

2. Forget normal shirts - smart stretchy tops and knitwear are your friend, as are wrap tops. You may want to invest in a range of vest top type things to wear underneath your hopefully growing wrap top/dress collection to preserve your modesty. Match these with a well fitting blazer you'll look perfectly smart & professional.

You should invest in a few well fitting blazers. Before you go shopping talk to a tailor to be clear on what parts of the blazer need to fit and what they can amend easily for you so you can get them tailored to fit you properly.

Finally, there are shops that cater specifically to busty ladies. If you insist on shirts they'll have some that are more likely to fit. They'll also be able to help with things like dresses. But really, just go with smart stretchy materials - life's too short.
posted by koahiatamadl at 7:36 AM on June 20, 2012

What not to wear covers all these issues. I'd watch as many episodes as you can.
posted by bananafish at 7:41 AM on June 20, 2012

J. Crew has great basic tees that work well for my short body. I'm large on top and small in the waist and I find that, with my diminutive stature, I have to wear pretty tight clothes or I look chunky. These tees come in xxs and fit very well - both long and short sleeve are available. I wear them constantly, and they're appropriate yet flattering.
posted by k8lin at 7:54 AM on June 20, 2012 [1 favorite]

The best-fitting/lasting jeans I've found for my waist-hip difference are Gap Curvy. If I were a bit smaller, I'd also be looking at Levi Curve as I've heard the very curvy style is fantastic (though the measurements stop a couple of sizes below Gap's, so I'm not sure if the curve thing makes them fit larger women better). Might not be useful for office-wear for you, but they're worth a look.

Bravissimo do shirts designed for a big bust - I don't need to wear office stuff to work but if I did I would be looking here. Not sure if they have a US store where you can try them on but they definitely ship there.

Also, cardigans are great! But make sure they are fitted rather than boxy (as someone the same height/size as my boyfriend, the trend for 'boyfriend' cardigans means that everything I try on just looks weird and ill-fitting). They're a good way to add a bit of colour - you can wear, say, a fuchsia cardi with a black wrap dress to make you warmer and look a bit brighter. I find thinner knits drape on me a bit better - I like cable knits, but on a big bust I end up with distorted lines and bobbles that look like knitted nipples.
posted by mippy at 8:00 AM on June 20, 2012

I will second Bravissimo (actually, their Pepperberry subsidiary) for button shirts. They're the only place I can find off-the-peg shirts to fit me.
posted by corvine at 8:10 AM on June 20, 2012

A possible source of inspiration, if you like it: I've always admired the Frocks section of the blog Some Girls Wander. I think I would actually describe it as 23 going on 60 -- she's a young attractive woman, and her style is ridiculously adorable and flattering, but it's definitely heavy on the cardigans and such.
posted by ootandaboot at 9:03 AM on June 20, 2012 [1 favorite]

I am quite a bit older than you--I was a teenager during the 80s preppy heyday--but have similar problems. Wrap and faux-wrap shirts with a camisole are your friends. Button shirts will need to be tailored. For jeans, I've had luck with Gap Curvy or Long & Lean, but also I just bought a pair of Not Your Daughter's Jeans that weren't too mom-like and fit great. (I wear my shirts untucked because I'm short waisted.)

I will also second the retro spots like Modcloth, Pinupgirl and Heartbreaker, but use the retro look in small doses so it stays classic instead of looking costumey. I also buy from Boden for for sort of a British equivalent of preppy-ness.

For a classic look, no 100% polyester, ever. Fewer pieces in better makes are your friends.

For shoes, I have the best luck with Born. Buy quality instead of cheap stuff. It shows.
posted by immlass at 9:19 AM on June 20, 2012 [1 favorite]

Do you know the blog Respect the Shoes? She has a great vintage-inflected style.
posted by Sidhedevil at 9:36 AM on June 20, 2012

You can easily have button-ups tailored to work with your physique. Best to buy a size larger, from what I understand. I have a couple of friends with amazing wardrobes who rely on this "trick".
posted by batmonkey at 9:47 AM on June 20, 2012

I'm busty with a waist. Sometimes I buy shirts that fit well across the chest and have them taken in -- usually, the tailor makes symmetrical adjustments to the back of the shirt. Other times, I buy a shirt that fits closely at the waist, and wear it with a tank top underneath. A solid or print tank can add color -- you don't have to buy those "fun" brightly printed tops that feel overly consipuous and not "you." By the way, you can wear a tank or cami under a well-fitting blouse, not just a too-small one :-)

Do you know what colors look especially good? If not, find out by holding fabrics of various colors near your face and looking in a mirror -- natural light it best, if possible. At first, you might just recognize a couple of colors that make a difference that you can see. It also helps to ask a friend or trustworthy relative to help.

I've recently started wearing scarves -- another great color-bringer. If a scarf has just one color found in your outfit, it can look like it belongs and pull things together. I've found wonderful scarves on Etsy. It's a bit difficult because there are thousands listed, but you'll get the hang of narrowing your search. I especially like hand-painted silks and and scarves made from vintage saris. There are many, many YouTube videos that show different ways to wear scarves.

You don't need a lot of makeup, but for me it helps to wear a "my lips but better" lipstick to add a little more contrast and brightness. Mascara is easy to wear and takes away some of the mousy look one can have if clothes are conservative and lashes are medium or light in color.

Finding jeans is hard! I like to wear jeans with a dark rinse because they don't look too casual. Since you say you tend to wear mom jeans, I suggest you try a pair that seem a bit too close-fitting. You'll get used to them, and besides, jeans usually stretch in the first hour or two of wear, and often after the first cold wash.
posted by wryly at 10:50 AM on June 20, 2012

The 100 by some woman who is on TV might give you some inspiration in building a classic wardrobe.

But you probably don't need a safari jacket.
posted by cyndigo at 11:43 AM on June 20, 2012

Cardigans, mom jeans, Dansko clogs, frumpy old-man sweaters and glasses -- the list goes on.

You're young so you can totally wear all this stuff. And glasses are cool. Just don't wear all the frumpy styles at the same time. Wear the vintage cardigan with stylish jeans or slim cropped trousers and sneakers/heels. Wear the mom jeans with cool shoes and a modern top. The Dansko clogs can be chic with a classic navy cashmere or merino v-neck and slim dark jeans. The stylists for the J Crew catalog are rather talented at taking "frumpy" things and making them look modern by pairing with unexpected colors and more tailored/feminine pieces and the models have nicely shaped brows, understated makeup, mascara, and some bright nail polish and/or lipstick. (I think some of their flashier things are not great quality but the slim tees and pencil skirts and button-downs are good, and cashmere when it's on sale.) So if you invest some time into the makeup/hair part of the look (the bright polish/lipstick is unnecessary, but being well groomed is) and put on skinny jeans or a cute skirt/tights, you can wear an oversized man's wool sweater without looking dowdy.

There is/was a fashion blogger thing about the "French wardrobe" which effectively was shorthand for shopping/dressing to aim at a chic, classic timeless style - A.P.C. type looks, good basics, not flashy - googling around will pull up some decent sites. I like Les ant-modernes for this kind of advice as well as the recent style guide book by Ines de la Fressange.
posted by citron at 8:40 PM on June 20, 2012 [2 favorites]